Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: halogenation versus oxidation.
Thionyl chloride (SOCl2) acts as halogenation reagent in its reaction with 1-[phenyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaborane 1a, b but unexpectedly behaves as an oxidant for 1-[2'-pyridyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaboranes 2a, b. The synthesis and characterization of all new compounds, including structure determinations of 1a, 2a, 1-[phenyl(chloro)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane 3a, and 1-[2'-pyridyl(oxo)methyl]-2-methyl-1,2-dicarba-closo-dodecaboranes 4a are reported and the possible pathways are discussed.
Terrasson
Vincent
V
Institut Lavoisier de Versailles-UMR CNRS 8180, Université de Versailles-Saint-Quentin-en-Yvelines, 45 avenue des Etats-Unis, 78035 Versailles, France.
Planas
José G
JG
Prim
Damien
D
Viñas
Clara
C
Teixidor
Francesc
F
Light
Mark E
ME
Hursthouse
Michael B
MB